Owner Direct Vacation
Rentals in Calvert County
The Best Owner Direct Vacation Rentals in Calvert County. Explore thousands of vacation home rentals, large cabins, and villas near Calvert County
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Explore the Best Calvert County Vacation Homes
Looking for the perfect place to stay in Calvert County? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Calvert County character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
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Find Calvert County Vacation Rentals
What makes our vacation homes stand out?

Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.

Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Calvert County
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Popular Neighborhoods for Calvert County Vacation Rentals
Discover the top neighborhoods in Calvert County and choose a place that suits your stay.
Dunkirk
Dunkirk VACATION RENTALSFridays Creek Winery
Fridays Creek Winery VACATION RENTALSCalvert Cliffs State Park
Calvert Cliffs State Park VACATION RENTALSChesapeake Beach
Chesapeake Beach VACATION RENTALSDowell
Dowell VACATION RENTALSPort Republic
Port Republic VACATION RENTALSPrince Frederick
Prince Frederick VACATION RENTALSCalvert Beach-Long Beach
Calvert Beach-Long Beach VACATION RENTALSNorth Beach
North Beach VACATION RENTALSChesapeake Ranch Estates-Drum Point
Chesapeake Ranch Estates-Drum Point VACATION RENTALSSt. Leonard
St. Leonard VACATION RENTALSMonday Jun 22
Calvert County, Maryland







Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Calvert County vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Calvert County
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How to Reserve Your Calvert County Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
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Check photos, reviews, and features for your top picks.
BOOK SECURELY
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Calvert County Vacation Rental FAQs
There are a lot of options in Calvert County. If you plan on staying in the Calvert County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Calvert County:
- Waterfront Cabin with Million Dollar View and Luxury Bath! Find Shark's Teeth!
- Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
- Waterfront Wildlife Retreat on the Patuxent River
- Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
- Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
- A breathtaking secluded luxury waterfront cottage, complete with a private pier.
- Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
- The Blue Crab Beach House - Free beach passes
- Bay view from Calvert Cliffs, Solomons Island & State Park nearby
- Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
There are 3 vacation rentals with private pools near Calvert County. Top-rated homes that have access to a swimming pool include:
If you are looking for a family-friendly vacation home in Calvert County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Calvert County:
Currently, the total number of properties listed in 2026 is over 261 in the Calvert County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Calvert County.